The copper catalyzed azide alkyne cycloaddition stands as one of the more prominent �click� reactions in chemistry, biochemistry, and material science. Its wide scope and reliability are hallmarks of this now-venerable transformation. The wide utility of this reaction notwithstanding, we have discovered that the rate of this reaction is dramatically affected by the presence of exogenous halides (NaI, NaBr, and NaCl). Since halides are present in many reaction mixtures and buffers used in the copper catalyzed azide alkyne cycloaddition, this finding is important in successful application of this transformation. Both mechanistic studies and applications to the synthesis of biomedically relevant triazoles will be discussed.

Halides inhibit the copper catalyzed azide alkyne cycloaddition

248th National Meeting (2014)

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